Like any good twenty-something “millennial” raised during the Disney Renaissance, Disney movies, books, toys, and vacations to Walt Disney World were a part of my upbringing that I cherish to this day. I think I managed to dress up as each princess throughout my childhood. For whatever reason, my mom even let me go to school in the 1st grade in my full Jasmine regalia (yes, it was a full shirt.) It wasn’t until high school that a friend in my class admitted she told her mom “Jasmine is in my class!” I wasn’t about to correct her…

We didn’t take our first family vacation to Walt Disney World until my brother and I were old enough to appreciate the trip and walk around ourselves sans clunky stroller, something I still admire my parents for doing. In 1999 we “Celebrated the Future Hand in Hand” during the Millennium Celebration with a stay at the Contemporary Hotel.

We’ve been visiting Walt Disney World every year since, in various family iterations. Like any obsessed Disney World family, we have our family favorite resorts, attractions and restaurants, we enjoy family inside jokes, and feel nostalgic and saddened when any drastic changes are made to change our idealized version of 1999 WDW. Despite the major changes since the Millennium celebration, we will always find ourselves planning another trip. I plan on continuing the tradition of a nearly-annual Disney trip for as long as possible, and I hope to attend with my own children in tow someday.

When was your first trip to Walt Disney World or Disneyland? What is your earliest and fondest memory of this trip?